Skip to content
2000
  1. Home
  2. A-Z Publications
  3. Current Chinese Chemistry
  4. Volume 2, Issue 3
  5. Article
Volume 2, Issue 3
  • ISSN: 2666-0016
  • E-ISSN: 2666-0008

Abstract

Benzimidazoles are important heterocyclic compounds having significant attention in the pharmacological industry due to their various biological and dying properties.

3-(1-benzo[]imidazol-2-yl)-2-chloroquinoline, a heterocyclic dye , was prepared using -phenylenediamine and 2-chloroquinoline-3-carbaldehyde in the presence of ceric ammonium nitrate catalyst and hydrogen peroxide under reflux condition, which was subjected to mordant and disperse dyeing study and antimicrobial activity to develop antimicrobial textile garment products.

Elemental analysis, NMR, FT-IR, Mass and UV-visible spectroscopic techniques were used to characterize dye . Polyester, wool and silk textile fabrics were selected for the evaluation of dyeing assessment of dispersed heterocyclic dye. The antimicrobial screening was done against , , , , , , and strains using standard drugs as reference.

The deep brown to green shades were observed for dye , particularly on polyester samples and showed excellent wash fastness and light fastness properties. Dye was active against showing 100 μgmL-1 MIC with 16.5 mm ZOI better than the reference drug ampicillin. It was more active against with 12.5, μgmL-1 MIC with 33 mm ZOI in compared to nystatin reference drug during antifungal screening. In primary screening, the MIC value for antimycobacterial activity was <12.5 μgmL-1.

The characteristics values of spectroscopic data support the chemical structure of dye . It may become the potent applicant for the production of antimicrobial textile garment products like socks, stockings, caps, . due to its fastness, lightning and antimicrobial activity results.

© 2022 Bentham Science Publishers
Loading

Article metrics loading...

/content/journals/ccchem/10.2174/2666001602666220819104427
2022-09-22
2025-03-17

  • From This Site

    /content/journals/ccchem/10.2174/2666001602666220819104427
    dcterms_title,dcterms_subject,pub_keyword
    -contentType:Contributor -contentType:Concept -contentType:Institution
    10
    5
Loading full text...

Full text loading...

References

  1. JohnB.W. The chemistry of the benzimidazoles.Chem. Rev.195148339754110.1021/cr60151a002
     [Google Scholar]
  2. GuzelB. AkgermanA. Mordant dyeing of wool by supercritical processing.J. Supercrit. Fluids200018324725210.1016/S0896‑8446(00)00065‑6
     [Google Scholar]
  3. ManianA.P. PaulR. BechtoldT. Metal mordanting in dyeing with natural colourants.Color. Technol.2016132210711310.1111/cote.12199
     [Google Scholar]
  4. Torres-GómezH. Hernández-NúñezE. León-RiveraI. Guerrero-AlvarezJ. Cedillo-RiveraR. Moo-PucR. Argotte-RamosR. Rodríguez-GutiérrezM.C. Chan-BacabM.J. Navarrete-VázquezG. Design, synthesis and in vitro antiprotozoal activity of benzimidazole-pentamidine hybrids.Bioorg. Med. Chem. Lett.200818113147315110.1016/j.bmcl.2008.05.00918486471
     [Google Scholar]
  5. MaderM. de DiosA. ShihC. BonjouklianR. LiT. WhiteW. López de UraldeB. Sánchez-MartinezC. del PradoM. JaramilloC. de DiegoE. Martín CabrejasL.M. DominguezC. MonteroC. ShepherdT. DallyR. TothJ.E. ChatterjeeA. PleiteS. Blanco-UrgoitiJ. PerezL. BarberisM. LoriteM.J. JambrinaE. NevillC.R.Jr LeeP.A. SchultzR.C. WolosJ.A. LiL.C. CampbellR.M. AndersonB.D. Imidazolyl benzimidazoles and imidazo[4,5-b]pyridines as potent p38α MAP kinase inhibitors with excellent in vivo antiinflammatory properties.Bioorg. Med. Chem. Lett.200818117918310.1016/j.bmcl.2007.10.10618039577
     [Google Scholar]
  6. KomazinG. PtakR.G. EmmerB.T. TownsendL.B. DrachJ.C. Resistance of human cytomegalovirus to D- and L-ribosyl benzimidazoles as a tool to identify potential targets for antiviral drugs.Nucleosides Nucleotides Nucleic Acids2003225-81725172710.1081/NCN‑12002312314565505
     [Google Scholar]
  7. RaoA. ChimirriA. De ClercqE. MonforteA.M. MonforteP. PannecouqueC. ZappalàM. Synthesis and anti-hIV activity of 1-(2,6-difluorophenyl)-1H,3H-thiazolo[3,4-a]benzimidazole structurally-related 1,2-substituted benzimidazoles.Farmaco2002571081982310.1016/S0014‑827X(02)01300‑912420877
     [Google Scholar]
  8. a SondhiS.M. RaniR. SinghJ. RoyP. AgrawalS.K. SaxenaA.K. Solvent free synthesis, anti-inflammatory and anticancer activity evaluation of tricyclic and tetracyclic benzimidazole derivatives.Bioorg. Med. Chem. Lett.20102072306231010.1016/j.bmcl.2010.01.14720188544
     [Google Scholar]
  9. b RefaatH.M. Synthesis and anticancer activity of some novel 2-substituted benzimidazole derivatives.Eur. J. Med. Chem.20104572949295610.1016/j.ejmech.2010.03.02220399544
     [Google Scholar]
  10. c ShaharyarM. AbdullahM.M. BakhtM.A. MajeedJ. Pyrazoline bearing benzimidazoles: Search for anticancer agent.Eur. J. Med. Chem.201045111411910.1016/j.ejmech.2009.09.03219883957
     [Google Scholar]
  11. d GellisA. KovacicH. BoufatahN. VanelleP. Synthesis and cytotoxicity evaluation of some benzimidazole-4,7-diones as bioreductive anticancer agents.Eur. J. Med. Chem.20084391858186410.1016/j.ejmech.2007.11.02018222567
     [Google Scholar]
  12. e ThimmegowdaN.R. Nanjunda SwamyS. KumarC.S.A. KumarY.C.S. ChandrappaS. YipG.W. RangappaK.S. Synthesis, characterization and evaluation of benzimidazole derivative and its precursors as inhibitors of MDA-MB-231 human breast cancer cell proliferation.Bioorg. Med. Chem. Lett.200818143243510.1016/j.bmcl.2007.08.07817981032
     [Google Scholar]
  13. f DemirayakS. Abu MohsenU. KuCağri KaraburunmarA. ynthesis and anticancer and anti-HIV testing of some pyrazino[1,2- a]benzimidazole derivatives.Eur. J. Med. Chem.200237325526010.1016/S0223‑5234(01)01313‑711900869
     [Google Scholar]
  14. PatilA. GangulyS. SuranaS. A systematic review of benzimidazole derivatives as an antiulcer agent.Rasayan J. Chem.20081447460
     [Google Scholar]
  15. KöhlerP. The biochemical basis of anthelmintic action and resistance.Int. J. Parasitol.200131433634510.1016/S0020‑7519(01)00131‑X11400692
     [Google Scholar]
  16. EvansB.E. RittleK.E. BockM.G. DiPardoR.M. FreidingerR.M. WhitterW.L. LundellG.F. VeberD.F. AndersonP.S. ChangR.S.L. LottiV.J. CerinoD.J. ChenT.B. KlingP.J. KunkelK.A. SpringerJ.P. HirshfieldJ. Methods for drug discovery: Development of potent, selective, orally effective cholecystokinin antagonists.J. Med. Chem.198831122235224610.1021/jm00120a0022848124
     [Google Scholar]
  17. HusainA. VarshneyM.M. RashidM. MishraR. AkhterA. Benzimidazole: A valuable insight into the recent advances and biological activities.J. Pharm. Res.201142413419
     [Google Scholar]
  18. WrightJ.B. The chemistry of benzimidazoles.Chem. Rev.1951483395541
     [Google Scholar]
  19. LawalA.S. NnadiwaC. Evaluation of wash and light fastness of some selected printed fabrics.ISOR-JPTE2014101-04
     [Google Scholar]
  20. PandaH. Modern Technology of Textile Dyes & PigmentsNIIR Project Consultancy Services, 2nd Edition, Dehli, India, 2003.
     [Google Scholar]
  21. FaddaA.A. EtmanH.A. AmerF.A. BarghoutM. MohamedKh.S. Azo disperse dyes for synthetic fibres. I: 2-Methyl- and 2-phenylquinazolone derivatives.J. Chem. Technol. Biotechnol.19956216516910.1002/jctb.280620209
     [Google Scholar]
  22. NawrockaW. SztubaB. KowalskaM.W. LiszkiewiczH. WietrzykJ. NasulewiczA. PełczyńskaM. OpolskiA. Synthesis and antiproliferative activity in vitro of 2-aminobenzimidazole derivatives.Farmaco2004592839110.1016/j.farmac.2003.12.00114871499
     [Google Scholar]
  23. HofmannK. Imidazole and its derivatives.New YorkWiley Interscience Publishers1953
     [Google Scholar]
  24. a MohanS. SundaraganesanN. MinkJ. FTIR and raman studies on benzimidazole.Spectrochim. Acta A19914781111111510.1016/0584‑8539(91)80042‑H
     [Google Scholar]
  25. b SundaraganesanN. IlakiamaniS. SubramaniP. JoshuaB.D. Comparison of experimental and ab initio HF and DFT vibrational spectra of benzimidazole.Spectrochim. Acta A Mol. Biomol. Spectrosc.2007673-462863510.1016/j.saa.2006.08.02016979935
     [Google Scholar]
  26. ÖzçelikS. GülA. Boronic ester of a phthalocyanine precursor with a salicylaldimino moiety.J. Organomet. Chem.2012699879110.1016/j.jorganchem.2011.11.016
     [Google Scholar]
/content/journals/ccchem/10.2174/2666001602666220819104427
Loading
Synthesis, Characterization, Textile Dyeing Study and Antimicrobial Activity of 3-(1H-benzo[d]imidazol-2-yl)-2-chloroquinoline
Curr Chin Chem 2, e190822207698 (2022); https://doi.org/10.2174/2666001602666220819104427
/content/journals/ccchem/10.2174/2666001602666220819104427
/content/journals/ccchem/10.2174/2666001602666220819104427
Loading

Data & Media loading...

Supplements

The general synthetic procedure, dyeing process, antimicrobial evaluation techniques and references related to these content are mentioned in Experimental part. FT-IR, GC-MS and NMR spectra are represented in Fig. to .

file format download Download

  • Article Type:     Rapid Communication
Keyword(s): Antimicrobial activity; benzimidazole; dyeing property; fastness properties; fluorescent; mordant textile dyeing

Most Cited Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error
Please enter a valid_number test